


Third Time's the Charm

by dictatoroffandoms



Category: Pocket Monsters: Sword & Shield | Pokemon Sword & Shield Versions
Genre: Other
Language: English
Status: Completed
Published: 2020-07-13
Updated: 2020-07-13
Packaged: 2021-03-05 02:34:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,367
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25246948
Author URL: https://archiveofourown.org/users/dictatoroffandoms/pseuds/dictatoroffandoms
Summary: Reader is not having a great evening, but the Chairman is, so he helps them have a little fun
Relationships: Rose | Chairman Rose/Reader
Kudos: 44





	Third Time's the Charm

**Author's Note:**

> This is a reader insert but I imagine that the reader character is about 25 or so, this is set after they would have graduated college. This also takes place before the game occurs.

“We can’t keep meeting like this, y/n.”

You look up from your drink, and turn on the bar stool to see who had just spoken. Much to your surprise, it was none other than -

“Chairman Rose, it’s always a pleasure,” you respond, a smile on your lips. You gesture to the empty seats at the bar next to you, indicating him to sit.

You are at a small bar, almost a members only sort of affair. It was meant to be a place to really get away for the rich and powerful. You get in because the owner is a close family friend, and you worked the bar during your college years. You’ve made small talk with many celebrities here, including the Chairman.

He slides onto a seat easier and waves at the bartender on duty. You look at the space behind him, expecting to Oleana, but there’s no one there. He must be really trying to keep a low profile if she’s not around.

As he orders a drink, you take another sip of your own. This is your second drink, and you’re taking your time with it. 

“So, how’s life?” you ask, purposefully keeping the question broad.

With a slight laugh, he answers, “ah, all things considered, quite good. I’m here tonight to celebrate actually.”

You make the ‘cheers’ motion with your drink, and sip again, “congratulations.”

He grins widely at the gesture, and returns it once he gets his drink. Neither of you speak, but the sounds of the bar around you keep the quiet at bay. 

This was probably the third time you’d met the Chairman at this bar. The first time, you were here just to relax after a long week at work while he was here with Oleana after a business deal went through, the second time you were here to quietly celebrate the new Champion Leon and he actually brought the Champion to the bar. It ended up being a bit of a crazy night then. It’s been several months since 

You’re fondly remembering that night, when he asks you a question. Shaking your head to clear your thoughts, you turn your attention back to reality. You offer an apologetic look, and he repeats the question.

“What brings you here?”

You bite your tongue. Your reason for being here is a bit embarrassing. However, for some reason you trust that Rose won’t tease you.

With a sigh you admit, “I was stood up, earlier this evening. My first dip back into dating, and it fell flat.”

You laugh to try and ease some of the tension you feel in your shoulders. Just thinking about having to sit there for an hour, miserable and alone, before realizing your date wasn’t going to show.

His face softens in sympathy, and you watch as a small crease forms in his brow. The gears are working in his mind, and as he comes up with a solution, his eyes light up. He whips his phone out and taps fervently at the screen.

Confusion is starting to show on your face, but he offers up no answers. Instead, he takes his drink, plucks the little umbrella from it and downs it as if it were a shot. 

“Finish your drink y/n.”

It was an odd request, you weren’t too sure of what was going on. You weren’t a reckless person, but if you were going to be reckless tonight would be the perfect night. He watches, a twinkle in his eyes.

He leaves a large bill on the counter, much too large for his one drink, and you move to get your wallet, but he puts a hand on yours, stopping you. You go to protest, but you are willing to accept his generosity. 

He takes your hand now, and helps you stand. Then he heads towards the door, you in town behind him. It’s easy to keep up with him, and you’re starting to feel adrenaline pump through your veins. 

Outside, there’s already a car waiting for the two of you, and the driver hops out to open both back doors. You sit on one side, and Rose gets in on the other. You have a million questions to ask, but you keep them to yourself, as surely they will all get answered, in time.

Without a word, the car takes off. You almost want to look out the window, try and track where you’re going, based on your knowledge of Wyndon, but Rose’s hand on your again brings your full attention to him. He traces small patterns on the back of your hand, and you relish in the feeling. You’d been single for far too long. You were also starting to feel the alcohol a little bit, and the back of your shirt clinging to you from the sweat. 

Just as you start to get antsy again, thinking about pulling out your phone, Rose’s hand on yours brings your attention back to him. He’s holding a flask now, you’re not sure when he pulled it out. He takes a drink and presses it into the hand he was holding. 

You take a sip from it. The flavor is like nothing you’ve had before, a bit sweet and earthy without being too strong. Without thinking, you take another sip, before passing it back. Rose can tell you're impressed, and seems glad to watch you enjoy.

The two of you pass the flask back and forth, and soon enough, the car rolls to a stop. The door opens, and you hold onto the exterior of the car as you step out. You really feel the alcohol now that you’re trying to stand. The ground feels like it’s coming up to meet your feet, and you have to focus very hard on staying upright. 

You venture a look at Rose, and it seems like he’s in no better shape. With the help of the driver, he slowly makes his way to you. Then together, you step into an elevator. You’re not really sure where you are, but most likely a parking garage, based on the smell. 

He leans heavily into the wall of the elevator, but you’re very determined to try and stand without aid. The elevator is very smooth, and you’re starting to get confident, just as it slows for the floor where you would be getting off. The sudden change of motion catches you off balance, and you fall into the Chairman’s arms.

Laughing, the two of you stay like that for a moment. But, Rose suddenly remembers what you’re here for and props you up. He rights himself and then the two of you manage to step off the elevator.

He guides you towards a large table. It’s been set, and has some very delicious smelling food laid out. Seeing it all stops you, confusion rising to the surface again. The realization hits you like a ton of bricks. You told Rose you had been stood up, and now you’re here and there’s this wonderful spread. You could cry. Rose senses the turmoil and helps you sit at the table. 

He pushes some water into your hand, and as he sits, drinks a large glass himself. You aren’t sure what emotion is on his face, but you can tell that all of this is meant to be genuine, and you really appreciate it.

Before you can speak your appreciation, he starts to speak, “everything here is delicious, but I highly recommend you try the spicy egg soup.” He points out the dish.

You reach for it, and dig in. It is better than anything you’ve ever tasted. You start to tuck into it earnestly now, and you hear a quiet laugh from Rose. The flavor doesn’t overpower your senses and you start to feel more steady as you eat. He’s also eating, some sort of curry, and you can tell both of you were hungry. As you both polish off your respective dishes, you meet each other’s eyes. 

There’s a tenderness in his eyes that you're not expecting. You don’t know him too well, but you are starting to want to get to know him more now. As you keep looking into his eyes, you can feel your face start to heat up. You weren’t really one to fuck on the first date, but this could be the time.

So, you rise from your seat, and make your way over to where Rose was seated. He raises his eyebrows, unsure of what you’re planning. Your steps are steady now, with more than just alcohol in your system. You reach his side quickly, and sit on a clear part of the table. The urge to kiss him is overwhelming, but you also don’t want to do anything unwanted.

Staying on the table like that, you take some finger food and eat a bite in front of him, then as casually as you can, offer some to him as well. There’s a new glint in his eyes as he leans forward to take the bite. As he takes the morsel into his mouth, his lips brush against your fingers, and you shiver at the feeling. The heat from your face rushes downward, and starts to pool in your gut. You move to copy the action, and as you turn to grab something else, you feel a featherlight hand rest cautiously on your thigh. 

You grab a piece of fruit, and turn back to Rose before taking a bite. It’s full of juice, so as your teeth pierce the skin, the sticky sweetness runs down your chin. The hand on your thigh tightens. You let a wicked smile grace your lips, and you offer the rest of the sticky fruit to Rose. He takes the entire bit in one bite. He chews it thoughtfully, but when you start to move your hand away, his other hand keeps it near. He swallows the food, then takes your sticky fingers into his mouth.

The sensation of his tongue on your digits makes you moan. You want to throw your head back and enjoy it, but his eyes keep seeking out yours. He thoroughly licks the juice from your fingers. You start to squirm on the table, seeking some other form of contact. Rose seemed to notice this, and he stands up, carefully letting your hand fall from his mouth. He uses both hands to spread your legs, and makes himself comfortable between them. You can feel his excitement pressed against your core, and the friction is heavenly. 

He shallowly thrusts against you, and you gasp. You’re starting to lose yourself to the feeling of pleasure, when he practically pins you to the table.

“My my y/n what a mess you’ve made of yourself, I’ll have to clean you up,” Rose’s voice was thick with desire.

With one hand he gently pushes your head back, and with the other he keeps your hands pinned. He starts to lick the juice that dripped down your chin. He makes his way down to where it had pooled near your collarbone, and laps at the small puddle. He ventures a kiss at the hollow of your neck, and sucks on the skin, just enough to leave a mark.

You practically thrash at the feeling of the kiss, so now inspired by your movement, he makes his way back up your neck. His kisses alter between chaste and intense and it keeps you on your toes. He uses the same that he pushed your head back with to now pull you into a kiss.

Your lips barely met his, and they were impossibly soft. With all the eagerness of a Yamper, you met his lips again, this time for a bruising kiss. The hand holding yours down relaxed, and you broke them free. One rested on his back, toying with his collar and you ran the other through his hair. Rose feeds off your eager energy and pulls you closer to the edge of the table, bringing your clothed bodies together.

When you pull apart for air, the tension in the air is suffocating. You place a hand on Rose’s chest, slightly pushing him back so you can cool off for a moment. He takes a full step back, and begins to remove his suit jacket. He lets it fall to the floor without grace. His tie is the next thing he starts to work on, and you watch entranced.

Leaving a trail of clothes, he moves towards another room, the bedroom presumably. You follow, playfully stepping around clothes as he continues to strip. At the door to the bedroom, you lose sight of him. You take the moment to completely undress, although unceremoniously. As you wait for Rose to return, you lay yourself out on the bed. It takes a moment, so you let one hand wander down and start to rub at yourself. 

You’ve barely started, when you feel Rose push your hand out of the way. You are about to say something witty in protest, when he replaces it with his mouth. Any words you had died in your throat and came out as a broken sound of pleasure instead.

His mouth on you feels like heaven, and you can’t help but to curl your fingers in his hair. You want to push him down, but the pleasure is already overwhelming enough as is. Back arching in pleasure, you’re feeling your orgasm inch closer and closer. A keening moan escapes you, and you can feel Rose laugh from where he is between your things. One particularly aimed lick from him has your hands flying from his hair to grip the sheets. You’re so close to orgasming, and you can feel a spew of words spilling from your mouth, when all of a sudden, Rose stops all movement.

The whine that follows is not a sound you’ll ever admit to making. He movies back from you, no touch at all left. You lift yourself up onto your elbows to see what he’s doing. His back is all you can see, as he rummages through a drawer on the far side of the room. Fighting off the haze from pleasure, you take this time to look around. The bedroom is very minimalist, the only decor being the occasional rose pattern. As you examine the room, Rose makes a small noise of triumph when he finds what he’s looking for, drawing your gaze back to him.

He’s holding a strip of condoms and a bottle of lube. You flush, the heat in your body beyond excited at the sight of them. Rose brings them over to the bedside table, he gets on the bed next to you, and slathers lube on his hand. He brings it between your legs, prodding at your sensitive entrance. He works on prepping you, and the stretch, while it does feel a bit rough, never actually hurts. He takes his time working you open, fingers languidly fucking you.

You start to squirm again, wanting something else, something more. Rose picks up on this, and takes his fingers from you. You know you ought to be giving attention to him, so you start to move over towards his cock. He hesitates, but your mouth is on him too fast for him to say anything. What you lack in experience in this sort of thing, you make up in eagerness.

It’s hard to take his length wholly into your mouth, you now know why he prepped you so well. Rose’s cock was incredibly thick, it made your jaw ache even with just the small length you had in your mouth. You had to use your hand to cover the rest of it. Sucking his dick was messy, but by the way his hands were gripping the sheets, he was feeling as much pleasure as you were before.

You fall into a rhythm with it, and as you do, you begin to hear these small but delicious noises from Rose. You come off his dick with a wet pop, and kiss at the juncture of his thigh. He whimpers a bit, but quickly leans up. You meet for a passionate kiss. He pushes you down gently and pulls away. He slips the condom quickly then makes himself comfortable between your legs. You wrap your legs around him and he brings himself to your entrance.

With a slow thrust, he sinks into you. You both are panting and moaning, and the gasp that escapes you when he bottoms out is positively sinful. You both pause for a moment here, adjusting to the feeling. As the moments pass by you can feel yourself getting used to the intrusion and starting to crave more. A minute twitch of your hips was all the encouragement that Rose needed to start thrusting.

The pace was slow at first, every little movement felt like electricity. One of your hands tangled into the sheets, and the other went up to hold Rose’s face close to yours. He leaned in a bit more, encouraged by your touch and your lips met. It was a hot kiss, desperate and full of the desire brought on by finally being together like this.

When the kiss broke, the pace went from slow to unrestrained. You moaned at the new feeling, and Rose’s hands gripped at your waist, just tight enough not to leave bruises. Wave after wave of pleasure washed over you and soon you were thrusting up to meet him halfway. 

The tension in your gut was at an all time high, and by the tightening of Rose’s grip, you could tell he was close too. You pull him into another kiss and arch up so as much of your bodies could touch, would. At that, Rose lost any sense of pace, his motions dissolving into erratic thrusts. Pulling Rose away from the kiss, you trail down his neck with wet warm kisses, until you reach the juncture between shoulder and neck. You kiss that spot twice, then when you feel yourself just about to cum, you bite down, hard. 

The bite makes Rose give one final thrust and pause while buried deep inside of you, you feel yourself wet and sticky in the aftermath of your own release. You make sure to kiss the spot again, ensuring it didn’t break the skin. The two of you lay together panting for a moment.

After you’ve caught your breath, you look up at Rose and laugh a little bit. It was hilarious how you found yourself in this situation. He gives you a smile and flops over beside you. It takes him a little longer to recover, having done most of the work, but eventually you hear him laugh as well. You turn on your side and plant a kiss on his cheek. 

At that, he blushes a bit, and gets up quickly. He takes care of the condom and brings back a warm wet rag to clean you both off. It's a nice aftercare ritual and once you’re both clean you head back out into the dining area to grab water for both of you. When you come back into the room, Rose seems surprised. You hand him the water, and sit on the edge of the bed. 

You take a sip of water before speaking, “it’s up to you if I stay…”

He stays quiet and drinks his own water as he’s thinking.

“But, if you want my input, I’d love to,” you add, wanting to let him know this doesn’t have to end so soon.

Instead of speaking, he simply opens up the covers on the side of the bed, and leans his toward it, motionning yo to join him. You slide into the bed and set your water down carefully. He lays one hand on you and gives you the brightest smile you’d seen all evening.

“I would love to enjoy your company more,” he says, also letting on that he’d like this to continue.

You weren’t how this would work out after tonight, but all you cared about at that moment was simply being in the company of the kindest man you’d ever met. 


End file.
